Patent IL-100807-A (IL)
Title: N-phenylcarbamate compounds, their preparation and fungicidal compositions containing them
IPC: C07D263/16
Filed: 1992-01-30
Abstract: N-phenylcarbamate compounds of the formula AZ-R3 NCO2R1R2 or their salts wherein R1 is a C1-3 alkyl group or a C1-3 alkyl group which is substituted by a chlorine atom; R2 is a hydrogen atom; a C3 alkenyl group; a C3-5 alkynyl group; a C1-3 alkyl group; a C1-3 alkyl group which is substituted by a C1-2 alkoxy group, a methoxyethoxy group, a methylthio group, a methoxycarbonyl group, a cyano group, a phenyl group or a fluorine atom; or a -COX1 group wherein X1 is a methoxy group, a cyclopropyl group, a C1-3 alkyl group or a C1-3 alkyl group which is substituted by a chlorine atom or a methoxy group; Z is a -CH2S- group; an -SCH2- group; a -CH2O- group; an -OCH2- group; a -CH=CH- group; a -CH2SO- group; a -CH2SO2- group; a -CH2SCH2- group; or a -CH2O-N=C(R4)- group; the right hyphen of each of which represents a bond directed toward R3; R3 is a phenyl group; a phenyl group which is substituted by one to three substituent(s) selected from the group consisting of a halogen atom, a trifluoromethyl group, a C1-2 alkylenedioxy group, a difluoromethylenedioxy group, a di-C1-2 alkylmethylenedioxy group, a methoxycarbonyl group, a 3-chloro- 5-trifluoromethyl-2-pyridyloxy group, a C1-3 alkyl group, a nitro group, a dimethylamino group, a trifluoromethanesulfonyloxy group, a C1-3 alkoxy group, a difluoromethoxy group, a methoxyimino-C1-2 alkyl group, a methylthio group, a dimethylcarbamoyloxy group, a cyano group, a phenyl group, a pyrrolyl group, a methylsulfinyl group and a methylsulfonyl group; a pyridyl group; a pyridyl group which is substituted by one or two substituent(s) selected from the group consisting of a chlorine atom, a trifluoromethyl group and a phenyl group; a benzothiazolyl group; a benzimidazolyl group which is substituted by a chlorine atom and a methyl group; a naphthyl group; a tetrahydronaphthyl group; a pyrimidinyl group which is substituted by a chlorine atom; a thienyl group; a thienyl group which is substituted by a chlorine atom; a furyl group; a thiazolinyl group which is substituted by a methyl group and a phenyl group; an oxazolinyl group which is substituted by a methyl group and a phenyl group; a quinolyl group which is substituted by a trifluoromethyl group; an indolyl group which is substituted by a methyl group; a pyrrolyl group which is substituted by a methyl group; a dihydrobenzofuryl group; an indanyl group; or benzoyl group; R4 is a hydrogen atom; a C1-2 alkyl group; a C1-2 alkyl group which is substituted by a fluorine atom; a cyclopropyl group; a methoxy group; a methylthio group; a phenyl group which is substituted by a trifluoromethyl group; a cyano group; an amino group; a morpholino group; or a methoxycarbonyl group; and A is a hydrogen atom; a halogen atom; a methyl group; a methoxy group; or a pyridyloxy group which is substituted by a chlorine atom and a trifluoromethyl group; provided (1) that R2 is a hydrogen atom when Z is a -CH2SO- group or a -CH2SO2- group, and (2) that an exception is made of the case (i) where R1 is a methyl group, R2 is a hydrogen atom and the -Z-R3 group is a styryl group or a 2-bromobenzyloxy group, the case (ii) where R1 is an ethyl group, R2 is a hydrogen atom and the -Z-R3 group is a benzyloxy group or a sytryl group, and the case (iii) where R1 is a methyl, ethyl or propyl group, R2 is a hydrogen atom and the -Z-R3 group is a 2-bromobenzylthio group.